Pyridine n-oxide compound and pest control agent

ABSTRACT

An object of the present invention is to provide a pyridine N-oxide compound that is excellent in pest control activity, particularly, insecticidal activity and/or acaricidal activity, is excellent in safety, and may be industrially advantageously synthesized. The pyridine N-oxide compound of the present invention is a compound of the formula (II), a stereoisomer, tautomer or hydrate thereof or a salt of any of these compounds, wherein R 1  represents a substituted or unsubstituted C1-6 alkylsulfonyl group; R 2  represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or the like; A 1  represents an oxygen atom, a sulfur atom, or the like; A 2  and A 3  each independently represent a carbon atom or a nitrogen atom; X represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or the like; and n represents an integer of 0 to 2.

TECHNICAL FIELD

The present invention relates to a pyridine N-oxide compound and a pest control agent. The present invention relates more specifically to a pyridine N-oxide compound that has excellent insecticidal activity and/or acaricidal activity, is excellent in safety, and may be industrially advantageously synthesized, and a pest control agent containing the same as an active ingredient. The present application claims the priority of Japanese Patent Application No. 2019-033373 filed on Feb. 26, 2019, the contents of which are incorporated herein.

BACKGROUND ART

Various compounds having insecticidal or acaricidal activity have been proposed. For practical use of such compounds as agrochemicals, it is required not only to have sufficiently high efficacy but to be less likely to cause chemical resistance, to cause neither phytotoxicity to plants nor soil pollution, and to be low toxic to livestock, fishes, etc.

Patent document 1 discloses a compound of formula (A), etc.

Patent Document 2 discloses a compound of formula (B), etc.

Patent Document 3 discloses a compound of formula (C), etc.

Patent Document 4 discloses a compound of formula (D), etc.

PRIOR ART DOCUMENTS Patent Documents Patent Document 1

-   International Publication No. WO 2017/146226A

Patent Document 2

-   International Publication No. WO 2016/121997A

Patent Document 3

-   International Publication No. WO 2016/026848A

Patent Document 4

-   International Publication No. WO 2016/104746A

SUMMARY OF THE INVENTION Object to be Solved by the Invention

An object of the present invention is to provide a pyridine N-oxide compound that is excellent in pest control activity, particularly, insecticidal activity and/or acaricidal activity, is excellent in safety, and may be industrially advantageously synthesized. Another object of the present invention is to provide a pest control agent, an insecticide or acaricide, an ectoparasite control agent, or an endoparasite control agent or expellant containing the pyridine N-oxide compound as an active ingredient.

Means to Solve the Object

As a result of diligent studies to attain the objects, the present invention including the following form has been completed.

[1] A compound of formula (II), a stereoisomer, tautomer or hydrate thereof or a salt of any of these compounds:

wherein

R¹ represents a substituted or unsubstituted C1-6 alkylsulfonyl group;

R² represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, or a halogeno group;

A¹ represents an oxygen atom, a sulfur atom, or NR³;

R³ represents a hydrogen atom or a C1-6 alkyl group;

A² and A³ each independently represent a carbon atom or a nitrogen atom;

X represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, or a substituted or unsubstituted C1-6 alkylsulfonyl group;

n represents a number of chemically acceptable Xs, and is an integer of 0 to 2; and Xs are the same or different when n is 2 or more.

[2] The compound according to the above [1], a stereoisomer, tautomer or hydrate thereof or a salt of any of these compounds, wherein the formula (II) is formula (I)

wherein R¹, R², X, and n represent the same meanings as described in the formula (II).

[3] A pest control agent comprising at least one active ingredient selected from the group consisting of a compound according to the above [1] to [2], a stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.

[4] An insecticide or acaricide comprising at least one active ingredient selected from the group consisting of a compound according to the above [1] to [2], a stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.

[5] An ectoparasite control agent comprising at least one active ingredient selected from the group consisting of a compound according to the above [1] to [2], a stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.

[6] An endoparasite control agent or expellant comprising at least one active ingredient selected from the group consisting of a compound according to the above [1] to [2], a stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.

[7] A soil treatment agent comprising at least one active ingredient selected from the group consisting of a compound according to the above [1] to [2], a stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.

Effect of the Invention

The pyridine N-oxide compound of the present invention may control pests that are problems associated with crops or hygiene. Particularly, the pyridine N-oxide compound of the present invention may effectively control agricultural insect pests and acari at a lower concentration. Furthermore, the pyridine N-oxide compound of the present invention may effectively control ectoparasites and endoparasites harmful to humans and animals. The pyridine N-oxide compound can also be used as a soil treatment agent.

MODE OF CARRYING OUT THE INVENTION [Pyridine N-Oxide Compound]

The pyridine N-oxide compound of the present invention is a compound of formula (II) (hereinafter, also referred to as compound (II)), tautomer or hydrate thereof or a salt of any of these compounds. The compound of formula (II) includes every stereoisomer which is an enantiomer or a diastereomer.

In the present invention, the term “unsubstituted” means a group consisting of only a mother nucleus. Only the name of a group consisting of a mother nucleus without the term “substituted” means an “unsubstituted” group unless otherwise specified.

On the other hand, the term “substituted” means that any hydrogen atom of a group consisting of a mother nucleus is substituted with a group (substituent) having a structure that is the same as or different from that of the mother nucleus. Thus, the “substituent” means another group bonded to the group consisting of a mother nucleus. The number of the substituent may be one or more. Two or more substituents are the same or different.

Terms such as “C1-6” mean that the number of carbon atoms in the group consisting of a mother nucleus is 1 to 6, etc. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified into a C2 alkoxy C4 alkyl group.

The “substituent” is not particularly limited as long as the substituent is chemically acceptable and produces the effect of the present invention. Hereinafter, a group capable of serving as the “substituent” is exemplified:

a C1-6 alkyl group such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group, and a n-hexyl group;

a C2-6 alkenyl group such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, and a 2-methyl-2-propenyl group;

a C2-6 alkynyl group such as an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, and a 1-methyl-2-propynyl group;

a C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cubanyl group;

a C6-10 aryl group such as a phenyl group and a naphthyl group;

a C6-10 aryl C1-6 alkyl group such as a benzyl group and a phenethyl group;

a 3- to 6-membered heterocyclyl group;

a 3- to 6-membered heterocyclyl C1-6 alkyl group;

a hydroxy group;

a C1-6 alkoxy group such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, and a t-butoxy group;

a C2-6 alkenyloxy group such as a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group;

a C2-6 alkynyloxy group such as an ethynyloxy group and a propargyloxy group;

a C6-10 aryloxy group such as a phenoxy group and a naphthoxy group;

a C6-10 aryl C1-6 alkoxy group such as a benzyloxy group and a phenethyloxy group;

a 5- or 6-membered heteroaryloxy group such as a thiazolyloxy group and a pyridyloxy group;

a 5- or 6-membered heteroaryl C1-6 alkyloxy group such as a thiazolylmethyloxy group and a pyridylmethyloxy group;

a formyl group;

a C1-6 alkylcarbonyl group such as an acetyl group and a propionyl group;

a formyloxy group;

a C1-6 alkylcarbonyloxy group such as an acetyloxy group and a propionyloxy group;

a C6-10 arylcarbonyl group such as a benzoyl group;

a C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an i-propoxycarbonyl group, a n-butoxycarbonyl group, and a t-butoxycarbonyl group;

a C1-6 alkoxycarbonyloxy group such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, a n-butoxycarbonyloxy group, and a t-butoxycarbonyloxy group;

a carboxy group;

a halogeno group such as a fluoro group, a chloro group, a bromo group, and an iodo group;

a C1-6 haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group, a 1-fluoro-n-butyl group, a perfluoro-n-pentyl group;

a C2-6 haloalkenyl group such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group;

a C2-6 haloalkynyl group such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group;

a C1-6 haloalkoxy group such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, and a 2,3-dichlorobutoxy group;

a C2-6 haloalkenyloxy group such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group;

a C1-6 haloalkylcarbonyl group such as a chloroacetyl group, a trifluoroacetyl group, and a trichloroacetyl group;

an amino group;

a C1-6 alkyl-substituted amino group such as a methylamino group, a dimethylamino group, and a diethylamino group;

a C6-10 arylamino group such as an anilino group and a naphthylamino group;

a C6-10 aryl C1-6 alkylamino group such as a benzylamino group and a phenethylamino group;

a formylamino group;

a C1-6 alkylcarbonylamino group such as an acetylamino group, a propanoylamino group, a butyrylamino group, and an i-propylcarbonylamino group;

a C1-6 alkoxycarbonylamino group such as a methoxycarbonylamino group, an ethoxycarbonylamino group, a n-propoxycarbonylamino group, and an i-propoxycarbonylamino group;

an unsubstituted or substituted aminocarbonyl group such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, and a N-phenyl-N-methylaminocarbonyl group;

an imino C1-6 alkyl group such as an iminomethyl group, a (1-imino)ethyl group, and a (1-imino)-n-propyl group;

a substituted or unsubstituted N-hydroxyimino C1-6 alkyl group such as a N-hydroxy-iminomethyl group, a (1-(N-hydroxy)-imino)ethyl group, a (1-(N-hydroxy)-imino)propyl group, a N-methoxy-iminomethyl group, and a (1-(N-methoxy)-imino)ethyl group;

an aminocarbonyloxy group;

a C1-6 alkyl-substituted aminocarbonyloxy group such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group;

a mercapto group;

a C1-6 alkylthio group such as a methylthio group, an ethylthio group, a n-propylthio group, an i-propylthio group, a n-butylthio group, an i-butylthio group, a s-butylthio group, and a t-butylthio group;

a C1-6 haloalkylthio group such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group;

a C6-10 arylthio group such as a phenylthio group and a naphthylthio group;

a 5- or 6-membered heteroarylthio group such as a thiazolylthio group and a pyridylthio group;

a C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group;

a C1-6 haloalkylsulfinyl group such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group;

a C6-10 arylsulfinyl group such as a phenylsulfinyl group;

a 5- or 6-membered heteroarylsulfinyl group such as a thiazolylsulfinyl group and a pyridylsulfinyl group;

a C1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group;

a C1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group;

a C6-10 arylsulfonyl group such as a phenylsulfonyl group;

a 5- or 6-membered heteroarylsulfonyl group such as a thiazolylsulfonyl group and a pyridylsulfonyl group;

a C1-6 alkylsulfonyloxy group such as a methylsulfonyloxy group, an ethylsulfonyloxy group, and a t-butylsulfonyloxy group;

a C1-6 haloalkylsulfonyloxy group such as a trifluoromethylsulfonyloxy group and a 2,2,2-trifluoroethylsulfonyloxy group;

a tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, and a t-butyldimethylsilyl group;

a tri-C6-10 aryl-substituted silyl group such as a triphenylsilyl group;

a cyano group;

and a nitro group.

For these “substituents”, any hydrogen atom in each substituent may be substituted with a group having a distinct structure. In this case, as the “substituent”, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, a nitro group or the like may be exemplified.

The “3- to 6-membered heterocyclyl group” described above contains 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. The heterocyclyl group may be either monocyclic or polycyclic. The polycyclic heterocyclyl group has at least one hetero ring, and the remaining ring(s) may be any of a saturated alicyclic ring, an unsaturated alicyclic ring and an aromatic ring. As the “3- to 6-membered heterocyclyl group”, a 3- to 6-membered saturated heterocyclyl group, a 5- or 6-membered heteroaryl group, a 5- or 6-membered partially unsaturated heterocyclyl group or the like may be exemplified.

As the 3- to 6-membered saturated heterocyclyl group, an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group or the like may be exemplified.

As the 5-membered heteroaryl group, a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, a tetrazolyl group or the like may be exemplified.

As the 6-membered heteroaryl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group or the like may be exemplified.

[R¹]

In the formula (II), R¹ represents a substituted or unsubstituted C1-6 alkylsulfonyl group.

As the “C1-6 alkylsulfonyl group” represented by R¹, a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group or the like may be exemplified.

As the substituent on the “C1-6 alkylsulfonyl group” represented by R¹, a halogeno group such as a fluoro group, a chloro group, a bromo group, and an iodo group may be preferably exemplified.

[R²]

In the formula (II), R² represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, or a halogeno group.

The “C1-6 alkyl group” represented by R² may be linear or branched. As the alkyl group, a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a s-butyl group, a t-butyl group, a n-pentyl group, an i-pentyl group, a neopentyl group, a n-hexyl group, an i-hexyl group, 2-methylbutyl group, or the like may be exemplified.

As a preferable substituent on the “C1-6 alkyl group” represented by R², a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a C1-6 alkoxy group such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, and a t-butoxy group; a C1-6 haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, and a trifluoromethoxy group; a cyano group; a 2-trimethylsilylethoxymethyl group; or the like may be exemplified.

As a preferable “substituted C1-6 alkyl group”, a C1-6 haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a pentafluoroethyl group, a 1,2-dichloro-n-propyl group, a 1,1,1,3,3,3-hexafluoropropan-2-yl group, a perfluoropropan-2-yl group, a 1-fluoro-n-butyl group, or a perfluoro-n-pentyl group may be exemplified.

As the “C3-8 cycloalkyl group” represented by R², a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cubanyl group or the like may be exemplified.

As the “C6-10 aryl group” represented by R², a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group or the like may be exemplified.

As the “5- to 6-membered heteroaryl group” represented by R², a 5-membered heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group; or a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group may be exemplified.

As the substituents on the “C3-8 cycloalkyl group”, the “C6-10 aryl group”, and the “5- to 6-membered heteroaryl group” represented by R², halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group, and a n-hexyl group; and a cyano group may be preferably exemplified.

As the “halogeno group” represented by R², a fluoro group, a chloro group, a bromo group, an iodo group or the like may be exemplified.

[A¹]

In the formula (II), A¹ represents an oxygen atom, a sulfur atom, or NR³. R³ represents a hydrogen atom, or a C1-6 alkyl group.

As the “C1-6 alkyl group” represented by R³, the same group as exemplified for R² above is exemplified.

[A² and A³]

In the formula (II), A² and A³ each independently represent a carbon atom or a nitrogen atom.

[X]

In the formula (II), X represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, or a substituted or unsubstituted C1-6 alkylsulfonyl group.

As the “substituted or unsubstituted C1-6 alkylsulfonyl group” represented by X, the same group as exemplified for R¹ may be exemplified.

As the “substituted or unsubstituted C1-6 alkyl group” represented by X, the same group as exemplified for R² above is exemplified.

As the “C1-6 alkoxy group” represented by X, a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, an i-butoxy group, a s-butoxy group, a t-butoxy group, a n-pentyloxy group, a n-hexyloxy group, an i-hexyloxy group or the like may be exemplified.

As the “C2-6 alkenyloxy group” represented by X, a vinyloxy group, an allyloxy group, a propenyloxy group, a butenyloxy group or the like may be exemplified.

As the “C2-6 alkynyloxy group” represented by X, an ethynyloxy group, a propargyloxy group or the like may be exemplified.

As the “C1-6 alkylthio group” represented by X, a methylthio group, an ethylthio group, a n-propylthio group, an i-propylthio group, a n-butylthio group, a n-pentylthio group, a n-hexylthio group or the like may be exemplified.

As the “C1-6 alkylsulfinyl group” represented by X, a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group or the like may be exemplified.

As the substituents on the “C1-6 alkoxy group”, the “C2-6 alkenyloxy group”, the “C2-6 alkynyloxy group”, the “C1-6 alkylthio group”, the “C1-6 alkylsulfinyl group”, and the “C1-6 alkylsulfonyl group” represented by X, halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group may be preferably exemplified.

[n]

In the formula (II), n represents a number of chemically acceptable Xs, and is an integer of 0 to 2; and Xs are the same or different when n is 2.

Specific examples of the compound of formula (II) will be shown in Tables 1 to 4. Table 1 shows the substituents of a compound of formula (III), Table 2 shows the substituents of a compound of formula (IV), Table 3 shows the substituents of a compound of formula (V), and Table 4 shows the substituents of a compound of formula (VI).

In the Tables, Me represents a methyl group, Et represents an ethyl group, ^(c)Pr represents a cyclopropyl group, and Ph represents a phenyl group.

TABLE 1 Compound No. R¹ R² A¹ (X)_(n) A-1 SO₂Et ^(c)Pr O 5-SO₂CF₃ A-2 SO₂Et ^(c)Pr O 5-CF₃ A-3 SO₂Et CF₃ O 5-SO₂CF₃ A-4 SO₂Et CF₃ O 5-CF₃ A-5 SO₂Et Ph O 5-SO₂CF₃ A-6 SO₂Et Ph O 5-CF₃ A-7 SO₂Et H O 5-SO₂CF₃ A-8 SO₂Et H O 5-CF₃ A-9 SO₂Et ^(c)Pr S 5-SO₂CF₃ A-10 SO₂Et ^(c)Pr S 5-CF₃ A-11 SO₂Et CF₃ S 5-SO₂CF₃ A-12 SO₂Et CF₃ S 5-CF₃ A-13 SO₂Et Ph S 5-SO₂CF₃ A-14 SO₂Et Ph S 5-CF₃ A-15 SO₂Et H S 5-SO₂CF₃ A-16 SO₂Et H S 5-CF₃ A-17 SO₂Et ^(c)Pr NMe 5-SO₂CF₃ A-18 SO₂Et ^(c)Pr NMe 5-CF₃ A-19 SO₂Et CF₃ NMe 5-SO₂CF₃ A-20 SO₂Et CF₃ NMe 5-CF₃ A-21 SO₂Et Ph NMe 5-SO₂CF₃ A-22 SO₂Et Ph NMe 5-CF₃ A-23 SO₂Et H NMe 5-SO₂CF₃ A-24 SO₂Et H NMe 5-CF₃

TABLE 2 Compound No. R¹ R² A¹ (X)_(n) B-1 SO₂Et ^(c)Pr O 5-SO₂CF₃ B-2 SO₂Et ^(c)Pr O 5-CF₃ B-3 SO₂Et CF₃ O 5-SO₂CF₃ B-4 SO₂Et CF₃ O 5-CF₃ B-5 SO₂Et Ph O 5-SO₂CF₃ B-6 SO₂Et Ph O 5-CF₃ B-7 SO₂Et H O 5-SO₂CF₃ B-8 SO₂Et H O 5-CF₃ B-9 SO₂Et ^(c)Pr S 5-SO₂CF₃ B-10 SO₂Et ^(c)Pr S 5-CF₃ B-11 SO₂Et CF₃ S 5-SO₂CF₃ B-12 SO₂Et CF₃ S 5-CF₃ B-13 SO₂Et Ph S 5-SO₂CF₃ B-14 SO₂Et Ph S 5-CF₃ B-15 SO₂Et H S 5-SO₂CF₃ B-16 SO₂Et H S 5-CF₃ B-17 SO₂Et ^(c)Pr NMe 5-SO₂CF₃ B-18 SO₂Et ^(c)Pr NMe 5-CF₃ B-19 SO₂Et CF₃ NMe 5-SO₂CF₃ B-20 SO₂Et CF₃ NMe 5-CF₃ B-21 SO₂Et Ph NMe 5-SO₂CF₃ B-22 SO₂Et Ph NMe 5-CF₃ B-23 SO₂Et H NMe 5-SO₂CF₃ B-24 SO₂Et H NMe 5-CF₃

TABLE 3 Compound No. R¹ R² A¹ (X)_(n) C-1 SO₂Et ^(c)Pr O 5-SO₂CF₃ C-2 SO₂Et ^(c)Pr O 5-CF₃ C-3 SO₂Et CF₃ O 5-SO₂CF₃ C-4 SO₂Et CF₃ O 5-CF₃ C-5 SO₂Et Ph O 5-SO₂CF₃ C-6 SO₂Et Ph O 5-CF₃ C-7 SO₂Et H O 5-SO₂CF₃ C-8 SO₂Et H O 5-CF₃ C-9 SO₂Et ^(c)Pr S 5-SO₂CF₃ C-10 SO₂Et ^(c)Pr S 5-CF₃ C-11 SO₂Et CF₃ S 5-SO₂CF₃ C-12 SO₂Et CF₃ S 5-CF₃ C-13 SO₂Et Ph S 5-SO₂CF₃ C-14 SO₂Et Ph S 5-CF₃ C-15 SO₂Et H S 5-SO₂CF₃ C-16 SO₂Et H S 5-CF₃ C-17 SO₂Et ^(c)Pr NMe 5-SO₂CF₃ C-18 SO₂Et ^(c)Pr NMe 5-CF₃ C-19 SO₂Et CF₃ NMe 5-SO₂CF₃ C-20 SO₂Et CF₃ NMe 5-CF₃ C-21 SO₂Et Ph NMe 5-SO₂CF₃ C-22 SO₂Et Ph NMe 5-CF₃ C-23 SO₂Et H NMe 5-SO₂CF₃ C-24 SO₂Et H NMe 5-CF₃

TABLE 4 Compound No. R¹ R² A¹ (X)_(n) D-1 SO₂Et ^(c)Pr O 5-SO₂CF₃ D-2 SO₂Et ^(c)Pr O 5-CF₃ D-3 SO₂Et CF₃ O 5-SO₂CF₃ D-4 SO₂Et CF₃ O 5-CF₃ D-5 SO₂Et Ph O 5-SO₂CF₃ D-6 SO₂Et Ph O 5-CF₃ D-7 SO₂Et H O 5-SO₂CF₃ D-8 SO₂Et H O 5-CF₃ D-9 SO₂Et ^(c)Pr S 5-SO₂CF₃ D-10 SO₂Et ^(c)Pr S 5-CF₃ D-11 SO₂Et CF₃ S 5-SO₂CF₃ D-12 SO₂Et CF₃ S 5-CF₃ D-13 SO₂Et Ph S 5-SO₂CF₃ D-14 SO₂Et Ph S 5-CF₃ D-15 SO₂Et H S 5-SO₂CF₃ D-16 SO₂Et H S 5-CF₃ D-17 SO₂Et ^(c)Pr NMe 5-SO₂CF₃ D-18 SO₂Et ^(c)Pr NMe 5-CF₃ D-19 SO₂Et CF₃ NMe 5-SO₂CF₃ D-20 SO₂Et CF₃ NMe 5-CF₃ D-21 SO₂Et Ph NMe 5-SO₂CF₃ D-22 SO₂Et Ph NMe 5-CF₃ D-23 SO₂Et H NMe 5-SO₂CF₃ D-24 SO₂Et H NMe 5-CF₃

A salt of the compound (II) or the like is not particularly limited as long as the salt is agriculturally or horticulturally acceptable. As the salt of the compound (II) or the like, for example, a salt of an inorganic acid such as hydrochloric acid and sulfuric acid; a salt of an organic acid such as acetic acid and lactic acid; a salt of an alkali metal such as lithium, sodium and potassium; a salt of an alkaline earth metal such as calcium and magnesium; a salt of a transition metal such as iron and copper; a salt of an organic base such as triethylamine, tributylamine, pyridine, and hydrazine; an ammonium salt; or the like may be exemplified.

[Compound of Formula (I)]

The compound of formula (II) is preferably a compound of formula (I).

In the formula (I), R¹, R², X, and n represent the same meanings as described in the formula (II).

In the formula (I), R¹ preferably represents an ethyl sulfonyl group. R² preferably represents a C3-8 cycloalkyl group, and more preferably represents a cyclopropyl group. X preferably represents a C1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group or 2,2,2-trifluoroethylsulfonyl group, and more preferably represents a trifluoromethylsulfonyl group. n preferably represents 1.

The pyridine N-oxide compound of the present invention (hereinafter occasionally described as a “compound of the present invention”) is not particularly limited by its manufacturing process. For example, the compound (I), a tautomer or hydrate thereof or a salt of any of these compounds may be obtained by known manufacturing process described in Examples, etc. Alternatively, the tautomer or hydrate of the compound (I) or a salt of any of these compounds may be obtained by a known approach from the compound (I).

The compound of the present invention is excellent in control effect on pests such as various agricultural insect pests affecting the growth of plants and acari.

Also, the compound of the present invention is a highly safe substance because of less phytotoxicity to crops and low toxicity to fishes and warm-blooded animals. Hence, the compound of the present invention is useful as an active ingredient for insecticides or acaricides.

Furthermore, in recent years, many insect pests such as diamondback moth, white-backed plant hopper, leafhopper, and aphid have developed resistance to various existing chemicals, causing problems of insufficient efficacy of these chemicals. Thus, chemicals effective for insect pests of resistant strains have been desired. The compound of the present invention exhibits an excellent control effect not only on sensitive strains but also on insect pests of various resistant strains and even acari of acaricide-resistant strains.

The compound of the present invention is excellent in control effect on ectoparasites and endoparasites harmful to humans and animals. Also, the compound of the present invention is a highly safe substance because of low toxicity to fishes and warm-blooded animals. Hence, the compound of the present invention is useful as an active ingredient for ectoparasite and endoparasite control agents.

The compound of the present invention exhibits efficacy at every developmental stage of organisms to be controlled, and exhibits an excellent control effect on, for example, eggs, nymphs, larvae, pupae, and adults of mites, insects, and the like.

[Pest Control Agent, Insecticide or Acaricide]

The pest control agent, or the insecticide or acaricide of the present invention contains at least one active ingredient selected from the pyridine N-oxide compounds of the present invention. The amount of the pyridine N-oxide compound contained in the pest control agent, or the insecticide or acaricide of the present invention is not particularly limited as long as its pest, agricultural insect pest or acari control effect is exhibited.

The pest control agent or the insecticide or acaricide of the present invention is preferably used for plants such as cereals; vegetables; root vegetables; tubers and roots; flowers and ornamental plants; fruit trees; ornamental foliage plants and trees of tea, coffee, cacao, and the like; feed crops; lawn grasses; and cotton.

In the application to plants, the pest control agent or the insecticide or acaricide of the present invention may be used for any site such as a leaf, a stem, a stalk, a flower, a bud, a fruit, a seed, a sprout, a root, a tuber, a tuberous root, a shoot, or a slip.

The pest control agent or the insecticide or acaricide of the present invention is not particularly limited by the species of the plant to which the pest control agent or the insecticide or acaricide is applied.

As the plant species, for example, an original species, a variant species, an improved variety, a cultivar, a mutant, a hybrid, a genetically modified organism (GMO) or the like may be exemplified.

The pest control agent of the present invention may be used in seed treatment, foliage application, soil application, submerged application, or the like in order to control various agricultural insect pests and acari.

Specific examples of various agricultural insect pests and acari controllable with the pest control agent of the present invention will be shown below.

(1) Butterflies or moths of the order Lepidoptera (a) moths of the family Arctiidae, for example, Hyphantria cunea and Lemyra imparilis; (b) moths of the family Bucculatricidae, for example, Bucculatrix pyrivorella; (c) moths of the family Carposinidae, for example, Carposina sasakii; (d) moths of the family Crambidae, for example, Diaphania indica and Diaphania nitidalis of Diaphania spp.; for example, Ostrinia furnacalis, Ostrinia nubilalis, and Ostrinia scapulalis of Ostrinia spp.; and Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Diatraea grandiosella, Glyphodes pyloalis, Hellula undalis, and Parapediasia teterrella; (e) moths of the family Gelechiidae, for example, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, and Sitotroga cerealella; (f) moths of the family Geometridae, for example, Ascotis selenaria; (g) moths of the family Gracillariidae, for example, Caloptilia theivora, Phyllocnistis citrella, and Phyllonorycter ringoniella; (h) butterflies of the family Hesperiidae, for example, Parnara guttata; (i) moths of the family Lasiocampidae, for example, Malacosoma neustria; (j) moths of the family Lymantriidae, for example, Lymantria dispar and Lymantria monacha of Lymantria spp.; and Euproctis pseudoconspersa and Orgyia thyellina; (k) moths of the family Lyonetiidae, for example, Lyonetia clerkella and Lyonetia prunifoliella malinella of Lyonetia spp.; (l) moths of the family Noctuidae, for example, Spodoptera depravata, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, and Spodoptera litura of Spodoptera spp.; for example, Autographa gamma and Autographa nigrisigna of Autographa spp.; for example, Agrotis ipsilon and Agrotis segetum of Agrotis spp.; for example, Helicoverpa armigera, Helicoverpa assulta, and Helicoverpa zea of Helicoverpa spp.; for example, Heliothis armigera and Heliothis virescens of Heliothis spp.; and Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, Naranga aenescens, Panolis japonica, Peridroma saucia, Pseudoplusia includens, and Trichoplusia ni; (m) moths of the family Nolidae, for example, Earias insulana; (n) butterflies of the family Pieridae, for example, Pieris brassicae and Pieris rapae crucivora of Pieris spp.; (o) moths of the family Plutellidae, for example, Acrolepiopsis sapporensis and Acrolepiopsis suzukiella of Acrolepiopsis spp.; and Plutella xylostella; (p) moths of the family Pyralidae, for example, Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, and Galleria mellonella; (q) moths of the family Sphingidae, for example, Manduca quinquemaculata and Manduca sexta of Manduca spp.; (r) moths of the family Stathmopodidae, for example, Stathmopoda masinissa; (s) moths of the family Tineidae, for example, Tinea translucens; (t) moths of the family Tortricidae, for example, Adoxophyes honmai and Adoxophyes orana of Adoxophyes spp.; for example, Archips breviplicanus and Archips fuscocupreanus of Archips spp.; and Choristoneura fumiferana, Cydia pomonella, Eupoecilia ambiguella, Grapholitha molesta, Homona magnanima, Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, and Sparganothis pilleriana; (u) moths of the family Yponomeutidae, for example, Argyresthia conjugella. (2) Insect pests of the order Thysanoptera (a) insect pests of the family Phlaeothripidae, for example, Ponticulothrips diospyrosi; (b) insect pests of the family Thripidae, for example, Frankliniella intonsa and Frankliniella occidentalis of Frankliniella spp.; for example, Thrips palmi and Thrips tabaci of Thrips spp.; and Heliothrips haemorrhoidalis and Scirtothrips dorsalis. (3) Insect pests of the order Hemiptera (A) the suborder Archaeorrhyncha (a) insect pests of the family Delphacidae, for example, Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, and Sogatella furcifera. (B) the suborder Clypeorrhyncha (a) insect pests of the family Cicadellidae, for example, Empoasca fabae, Empoasca nipponica, Empoasca onukii, and Empoasca sakaii of Empoasca spp.; and Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus, Macrosteles striifrons, and Nephotettix cinctinceps. (C) the suborder Heteroptera (a) insect pests of the family Alydidae, for example, Riptortus clavatus; (b) insect pests of the family Coreidae, for example, Cletus punctiger and Leptocorisa chinensis; (c) insect pests of the family Lygaeidae, for example, Blissus leucopterus, Cavelerius saccharivorus, and Togo hemipterus; (d) insect pests of the family Miridae, for example, Halticus insularis, Lygus lineolaris, Psuedatomoscelis seriatus, Stenodema sibiricum, Stenotus rubrovittatus, and Trigonotylus caelestialium; (e) insect pests of the family Pentatomidae, for example, Nezara antennata and Nezara viridula of Nezara spp.; for example, Eysarcoris aeneus, Eysarcoris lewisi, and Eysarcoris ventralis of Eysarcoris spp.; and Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, Halyomorpha halys, Piezodorus hybneri, Plautia crossota, and Scotinophora lurida; (f) insect pests of the family Pyrrhocoridae, for example, Dysdercus cingulatus; (g) insect pests of the family Rhopalidae, for example, Rhopalusmsculatus; (h) insect pests of the family Scutelleridae, for example, Eurygasterintegriceps; (i) insect pests of the family Tingidae, for example, Stephanitis nashi. (D) the suborder Sternorrhyncha (a) insect pests of the family Adelgidae, for example, Adelges laricis; (b) insect pests of the family Aleyrodidae, for example, Bemisia argentifolii and Bemisia tabaci of Bemisia spp.; and Aleurocanthus spiniferus, Dialeurodes citri, and Trialeurodes vaporariorum; (c) insect pests of the family Aphididae, for example, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis pomi, Aphis sambuci, and Aphis spiraecola of Aphis spp.; for example, Rhopalosiphum maidis and Rhopalosiphum padi of Rhopalosiphum spp.; for example, Dysaphis plantaginea and Dysaphis radicola of Dysaphis spp.; for example, Macrosiphum avenae and Macrosiphum euphorbiae of Macrosiphum spp.; for example, Myzus cerasi, Myzus persicae, and Myzus varians of Myzus spp.; and Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Chaetosiphon fragaefolii, Hyalopterus pruni, Hyperomyzus lactucae, Lipaphis erysimi, Megoura viciae, Metopolophium dirhodum, Nasonovia ribis-nigri, Phorodon humuli, Schizaphis graminum, Sitobion avenae, and Toxoptera aurantii; (d) insect pests of the family Coccidae, for example, Ceroplastes ceriferus and Ceroplastes rubens of Ceroplastes spp.; (e) insect pests of the family Diaspididae, Pseudaulacaspis pentagona and Pseudaulacaspis prunicola of Pseudaulacaspis spp.; for example, Unaspis euonymi and Unaspis yanonensis of Unaspis spp.; and Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, and Pseudaonidia paeoniae; (f) insect pests of the family Margarodidae, for example, Drosicha corpulenta and Icerya purchasi; (g) insect pests of the family Phylloxeridae, for example, Viteus vitifolii; (h) insect pests of the family Pseudococcidae, for example, Planococcus citri and Planococcus kuraunhiae of Planococcus spp.; and Phenacoccus solani and Pseudococcus comstocki; (i) insect pests of the family Psyllidae, for example, Psylla mali and Psylla pyrisuga of Psylla spp.; and Diaphorina citri. (4) Insect pests of the suborder Polyphaga (a) insect pests of the family Anobiidae, for example, Lasioderma serricorne; (b) insect pests of the family Attelabidae, for example, Byctiscus betulae and Rhynchites heros; (c) insect pests of the family Bostrichidae, for example, Lyctus brunneus; (d) insect pests of the family Brentidae, for example, Cylas formicarius; (e) insect pests of the family Buprestidae, for example, Agrilus sinuatus; (f) insect pests of the family Cerambycidae, for example, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, and Xylotrechus pyrrhoderus; (g) insect pests of the family Chrysomelidae, for example, Bruchus pisorum and Bruchus rufimanus of Bruchus spp.; for example, Diabrotica barberi, Diabrotica undecimpunctata, and Diabrotica virgifera of Diabrotica spp.; for example, Rhyllotreta nemorum and Rhyllotreta striolata of Phyllotreta spp.; and Aulacophora femoralis, Callosobruchus chinensis, Cassida nebulosa, Chaetocnema concinna, Leptinotarsa decemlineata, Oulema oryzae, and Psylliodes angusticollis; (h) insect pests of the family Coccinellidae, for example, Epilachna varivestis and Epilachna vigintioctopunctata of Epilachna spp.; (i) insect pests of the family Curculionidae, for example, Anthonomus grandis and Anthonomus pomorum of Anthonomus spp.; for example, Sitophilus granarius and Sitophilus zeamais of Sitophilus spp.; and Echinocnemus squameus, Euscepes postfasciatus, Hylobius abietis, Hypera postica, Lissohoptrus oryzophilus, Otiorhynchus sulcatus, Sitona lineatus, and Sphenophorus venatus; (j) insect pests of the family Elateridae, for example, Melanotus fortnumi and Melanotus tamsuyensis of Melanotus spp.; (k) insect pests of the family Nitidulidae, for example, Epuraea domina; (l) insect pests of the family Scarabaeidae, for example, Anomala cuprea and Anomala rufocuprea of Anomala spp.; and Cetonia aurata, Gametis jucunda, Heptophylla picea, Melolontha melolontha, and Popillia japonica; (m) insect pests of the family Scolytidae, for example, Ips typographus; (n) insect pests of the family Staphylinidae, for example, Paederus fuscipes; (o) insect pests of the family Tenebrionidae, for example, Tenebrio molitor and Tribolium castaneum; (p) insect pests of the family Trogossitidae, for example, Tenebroides mauritanicus. (5) Insect pests of the order Diptera (A) the suborder Brachycera (a) insect pests of the family Agromyzidae, for example, Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, and Liriomyza trifolii of Liriomyza spp.; and Chromatomyia horticola and Agromyza oryzae; (b) insect pests of the family Anthomyiidae, for example, Delia platura and Delia radicum of Delia spp.; and Pegomya cunicularia; (c) insect pests of the family Drosophilidae, for example, Drosophila melanogaster and Drosophila suzukii of Drosophila spp.; (d) insect pests of the family Ephydridae, for example, Hydrellia griseola; (e) insect pests of the family Psilidae, for example, Psila rosae; (f) insect pests of the family Tephritidae, for example, Bactrocera cucurbitae and Bactrocera dorsalis of Bactrocera spp.; for example, Rhagoletis cerasi and Rhagoletis pomonella of Rhagoletis spp.; and Ceratitis capitata and Dacus oleae. (B) the suborder Nematocera (a) insect pests of the family Cecidomyiidae, for example, Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor, and Sitodiplosis mosellana. (6) Insect pests of the order Orthoptera (a) insect pests of the family Acrididae, for example, Schistocerca americana and Schistocerca gregaria of Schistocerca spp.; and Chortoicetes terminifera, Dociostaurus maroccanus, Locusta migratoria, Locustana pardalina, Nomadacris septemfasciata, and Oxya yezoensis; (b) insect pests of the family Gryllidae, for example, Acheta domestica and Teleogryllus emma; (c) insect pests of the family Gryllotalpidae, for example, Gryllotalpa orientalis; (d) insect pests of the family Tettigoniidae, for example, Tachycines asynamorus.

(7) Acari

(A) Acaridida of the order Astigmata (a) mites of the family Acaridae, for example, Rhizoglyphus echinopus and Rhizoglyphus robini of Rhizoglyphus spp.; for example, Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, and Tyrophagus similis of Tyrophagus spp.; and Acarus siro, Aleuroglyphus ovatus, and Mycetoglyphus fungivorus; (B) Actinedida of the order Prostigmata (a) mites of the family Tetranychidae, for example, Bryobia praetiosa and Bryobia rubrioculus of Bryobia spp.; for example, Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis, Eotetranychus geniculatus, Eotetranychus kankitus, Eotetranychus pruni, Eotetranychus shii, Eotetranychus smithi, Eotetranychus suginamensis, and Eotetranychus uncatus of Eotetranychus spp.; for example, Oligonychus hondoensis, Oligonychus ilicis, Oligonychus karamatus, Oligonychus mangiferus, Oligonychus orthius, Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, and Oligonychus ununguis of Oligonychus spp.; for example, Panonychus citri, Panonychus mori, and Panonychus ulmi of Panonychus spp.; for example, Tetranychus cinnabarinus, Tetranychus evansi, Tetranychus kanzawai, Tetranychus ludeni, Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, and Tetranychus viennensis of Tetranychus spp.; for example, Aponychus corpuzae and Aponychus firmianae of Aponychus spp.; for example, Sasanychus akitanus and Sasanychus pusillus of Sasanychus spp.; for example, Schizotetranychus celarius, Schizotetranychus longus, Schizotetranychus miscanthi, Schizotetranychus recki, and Schizotetranychus schizopus of Schizotetranychus spp.; and Tetranychina harti, Tuckerella pavoniformis, and Yezonychus sapporensis; (b) mites of the family Tenuipalpidae, for example, Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus russulus, and Brevipalpus californicus of Brevipalpus spp.; for example, Tenuipalpus pacificus and Tenuipalpus zhizhilashviliae of Tenuipalpus spp.; and Dolichotetranychus floridanus; (c) mites of the family Eriophyidae, for example, Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Aceria paradianthi, Aceria tiyingi, Aceria tulipae, and Aceria zoysiea of Aceria spp.; for example, Eriophyes chibaensis and Eriophyes emarginatae of Eriophyes spp.; for example, Aculops lycopersici and Aculops pelekassi of Aculops spp.; for example, Aculus fockeui and Aculus schlechtendali of Aculus spp.; and Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepitrimerus vitis, Epitrimerus pyri, Paraphytoptus kikus, Paracalacarus podocarpi, and Phyllocotruta citri; (d) mites of the family Tarsonemidae, for example, Tarsonemus bilobatus and Tarsonemus waitei of Tarsonemus spp.; and Phytonemus pallidus and Polyphagotarsonemus latus; (e) mites of the family Penthaleidae, for example, Penthaleus erythrocephalus and Penthaleus major of Penthaleus spp.

The pest control agent of the present invention may be used as a mixture or in combination with another active ingredient such as a fungicide, an insecticide or acaricide, a nematicide, or a pesticide for soil insect pests; a plant regulating agent, a synergist, a fertilizer, a soil improvement agent, animal feed, or the like.

The combination of the compound of the present invention with another active ingredient may be expected to have synergistic effects on insecticidal, acaricidal, or nematicidal activity. The synergistic effects may be confirmed by the equation of Colby (Colby. S. R.; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, p. 20-22, 1967) according to a standard method.

Specific examples of the insecticide or acaricide, the nematicide, the pesticide for soil insect pests, the anthelmintic agent, and the like that may be used as a mixture or in combination with the pest control agent of the present invention will be shown below.

(1) Acetylcholinesterase inhibitors:

(a) carbamate-based: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb, fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, allyxycarb, aminocarb, bufencarb, cloethocarb, metam-sodium, and promecarb;

(b) organophosphorus-based: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isocarbophos, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanofenphos, CYAP, demeton-S-methyl sulfone, dialifos, dichlofenthion, dioxabenzofos, etrimfos, fensulfothion, flupyrazofos, fonofos, formothion, fosmethilan, isazofos, jodfenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propaphos, prothoate, and sulprofos.

(2) GABA-ergic chloride ion channel antagonists: acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole, camphechlor, heptachlor, and dienochlor. (3) Sodium channel modulators: acrinathrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-Isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrins, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpirithrin, flubrocythrinate, flufenprox, metofluthrin, protrifenbute, pyresmethrin, and terallethrin. (4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifurone, and flupyrimine. (5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram and spinosad. (6) Chloride channel activators: abamectin, emamectin-benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, and nemadectin. (7) Juvenile hormone-like substances: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen, diofenolan, epofenonane, and triprene. (8) Other nonspecific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, and tartar emetic. (9) Homoptera selective feeding inhibitors: flonicamid, pymetrozine, and pyrifluquinazon. (10) acari growth inhibitors: clofentezine, diflovidazin, hexythiazox, and etoxazole. (11) Insect midgut inner membrane disrupting agents derived from microorganisms: Bacillus thuringiensis subsp. Israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, and Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, and Cry34Ab1/Cry35Ab1. (12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, and tetradifon. (13) Oxidative phosphorylation uncouplers: chlorfenapyr, sulfluramid, DNOC, binapacryl, dinobuton, and dinocap. (14) Nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride, nereistoxin, thiosultap-sodium, and thiocyclam. (15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, and fluazuron. (16) Diptera molting disrupting agents: cyromazine. (17) Molting hormone receptor agonists: chromafenozide, halofenozide, methoxyfenozide, and tebufenozide. (18) Octopamine receptor agonists: amitraz, demiditraz, and chlordimeform. (19) Mitochondrial electron transport system complex III inhibitors: acequinocyl, fluacrypyrim, and hydramethylnon. (20) Mitochondrial electron transport system complex I inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, and rotenone. (21) Voltage-gated sodium channel blockers: indoxacarb and metaflumizone. (22) Acetyl CoA carboxylase inhibitors: spirodiclofen, spiromesifen, and spirotetramat. (23) Mitochondrial electron transport system complex IV inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, and cyanide. (24) Mitochondrial electron transport system complex II inhibitors: cyenopyrafen, cyflumetofen, and pyflubumide. (25) Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, and tetraniliprole. (26) Mixed function oxidase inhibitor compounds: piperonyl butoxide. (27) Latrophilin receptor agonists: depsipeptide, cyclodepsipeptide, 24 membered cyclodepsipeptide, and emodepside. (28) Other agents (based on an unknown mechanism of action): azadirachtin, benzoximate, bifenazate, bromopropylate, quinomethionate, cryolite, dicofol, pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate, metaldehyde, chlorobenzilate, clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossyplure, japonilure, metoxadiazone, oil, potassium oleate, tetrasul, triarathene, afidopyropen, flometoquin, flufiprole, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecanamide, fluralaner, afoxolaner, fluxametamide, 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-(1H-1,2,4-triazole-1-yl)benzonitrile (CAS: 943137-49-3), broflanilide, other m-diamides, Steinernema carpocapsae, Steinernema glaseri, Pasteuria penetrans, Paecilomyces tenuipes, Paecilomyces fumosoroseus, Beauveria bassiana, Beauveria brongniartii, Metarhizium anisopliae, Verticillium lecanii, and acynonapyr. (29) Anthelmintic agents: (a) benzimidazole-based: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, parbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, and cambendazole; (b) salicylanilide-based: closantel, oxyclozanide, rafoxanide, and niclosamide; (c) substituted phenol-based: nitroxinil and nitroscanate; (d) pyrimidine-based: pyrantel and morantel; (e) imidazothiazole-based: levamisole and tetramisole; (f) tetrahydropyrimidine-based: praziquantel and epsiprantel; (g) other anthelmintic agents: cyclodiene, ryania, clorsulon, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetarsamide, melarsomine, and arsenamide.

Specific examples of the fungicide that may be used as a mixture or in combination with the pest control agent of the present invention will be shown below.

(1) Nucleic acid biosynthesis inhibitors:

(a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clozylacon, and ofurace;

(b) adenosine deaminase inhibitors: bupirimate, dimethirimol, and ethirimol;

(c) DNA/RNA synthesis inhibitors: hymexazol and octhilinone;

(d) DNA topoisomerase II inhibitors: oxolinic acid.

(2) Mitotic inhibitors and cell division inhibitors:

(a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorfenazole, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, and ethaboxam;

(b) cell division inhibitors: pencycuron;

(c) spectrin-like protein delocalization inhibitors: fluopicolide.

(3) Respiration inhibitors:

(a) complex I NADH oxidation-reduction enzyme inhibitors: diflumetorim and tolfenpyrad;

(b) complex II succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil, isofetamid, fluopyram, fenfuram, furmecyclox, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pyraziflumid, pydiflumetofen, isoflucypram, and inpyrfluxam;

(c) complex III ubiquinol oxidase Qo inhibitors: azoxystrobin, coumoxystrobin, coumethoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxim-methyl, trifloxystrobin, dimoxystrobin, fenaminstrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, pyribencarb, mandestrobin and metyltetraprole;

(d) complex III ubiquinol reductase Qi inhibitors: cyazofamid, amisulbrom, and fenpicoxamid;

(e) oxidative phosphorylation uncoupling agents: binapacryl, meptyldinocap, dinocap, fluazinam, and ferimzone;

(f) oxidative phosphorylation inhibitors (ATP synthase inhibitors): fentin acetate, fentin chloride, and fentin hydroxide;

(g) ATP production inhibitors: silthiofam;

(h) complex III: Qx (unknown) inhibitor of cytochrome bcl (ubiquinone reductase): ametoctradin.

(4) Amino acid and protein synthesis inhibitors

(a) methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim, and pyrimethanil;

(b) protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, and oxytetracycline.

(5) Signal transduction inhibitors:

(a) signal transduction inhibitors: quinoxyfen and proquinazid;

(b) MAP/histidine kinase inhibitors in osmotic signal transduction: fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone, and vinclozolin.

(6) Lipid and cell membrane synthesis inhibitors:

(a) phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos, and isoprothiolane;

(b) lipid peroxidation agents: biphenyl, chloroneb, dichloran, quintozene, tecnazene, tolclofos-methyl, and etridiazole;

(c) agents that act on cell membranes: iodocarb, propamocarb, propamocarb-hydrochloride, propamocarb-fosetylate, and prothiocarb;

(d) microorganisms that disrupt cell membranes of pathogens: Bacillus subtilis, Bacillus subtilis strain QST713 strain, Bacillus subtilis FZB24, Bacillus subtilis strain MBI600, Bacillus subtilis strain D747, and Bacillus amyloliquefaciens;

(e) agents that disrupt cell membranes: Melaleuca alternifolia (tea tree) extract.

(7) Cell membrane sterol biosynthesis inhibitors:

(a) C14-demethylation inhibitors in sterol biosynthesis: triforine, pyrifenox, pyrisoxazole, fenarimol, flurprimidol, nuarimol, imazalil, imazalil-sulfate, oxpoconazole fumarate, pefurazoate, prochloraz, triflumizole, viniconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, fluquinconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole and mefentrifluconazole;

(b) Δ14 reductase and sterol Δ8→Δ7-isomerase inhibitors in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, and spiroxamine;

(c) 3-keto reductase inhibitors in C4-demethylation in the sterol biosynthesis system: fenhexamid and fenpyrazamine;

(d) squalene epoxidase inhibitors in the sterol biosynthesis system: pyributicarb, naftifine, and terbinafine.

(8) Cell wall synthesis inhibitors

(a) trehalase inhibitors: validamycin;

(b) chitin synthase inhibitors: polyoxins and polyoxorim;

(c) cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph, benthiavalicarb-isopropyl, iprovalicarb, valifenalate, and mandipropamid.

(9) Melanin biosynthesis inhibitors

(a) melanin biosynthesis reductase inhibitors: fthalide, pyroquilon, and tricyclazole;

(b) melanin biosynthesis anhydrase inhibitors: carpropamid, diclocymet, and fenoxanil;

(c) melanin biosynthesis polyketide synthesis inhibitors: tolprocarb.

(10) Host plant resistance inducers:

(a) agents that act on salicylic acid synthesis pathway: acibenzolar-S-methyl;

(b) others: probenazole, tiadinil, isotianil, dichlobentiazox, laminarin, and Reynoutria sachalinensis extract.

(11) Agents with unknown mode of action: cymoxanil, fosetyl-aluminum, phosphoric acid (phosphate), tecloftalam, triazoxide, flusulfamide, diclomezine, methasulfocarb, cyflufenamid, metrafenone, pyriofenone, dodine, dodine free base, and flutianil. (12) Agents having multiple active sites: copper (copper salt), bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, ferbam, mancozeb, maneb, mancopper, metiram, polycarbamate, propineb, thiram, zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine, iminoctadine triacetate, iminoctadine trialbesilate, anilazine, dithianon, quinomethionate, and fluoroimide. (13) Other agents: DBEDC, fluorofolpet, guazatine acetate, bis(8-quinolinolato)copper (II), propamidine, chloropicrin, cyprofuram, agrobacterium, bethoxazin, diphenylamine, methyl isothiocyanate (MITC), mildiomycin, capsaicin, cufraneb, cyprosulfamide, dazomet, debacarb, dichlorophen, flumetover, fosetyl-calcium, fosetyl-sodium, irumamycin, natamycin, nitrothal isopropyl, oxamocarb, pyrrolnitrin, tebufloquin, tolnifanide, zarilamide, algophase, amicarthiazol, oxathiapiprolin, metiram zinc, benthiazole, trichlamide, uniconazole, oxyfenthiin, picarbutrazox, dichlobentiazox, quinofumelin, thiuram, ambam, Agrobacterium radiobacter, Coniothyrium minitans, Pseudomonas fluorescens, Pseudomonas rhodesiae, Talaromyces flavus, Trichoderma atroviride, Erwinia carotovora subsp. carotovora, Bacillus simplex, Variovorax paradoxus, Lactobacillus plantarum, florylpicoxamid, pyrapropoyne, fluindapyr, aminopyrifen, pyridachlometyl, and ipflufenoquin.

Specific examples of the plant regulating agent that may be used as a mixture or in combination with the pest control agent of the present invention will be shown below.

Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl aminoethoxyvinyl glycine (also called aviglycine), aminooxyacetate, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyrate, dichlorprop, phenothiol, 1-naphthyl acetamide, ethychlozate, cloxyfonac, maleic acid hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (−)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-amino levulinic acid, and daminozide.

[Ectoparasite Control Agent]

The ectoparasite control agent of the present invention contains at least one active ingredient selected from the pyridine N-oxide compounds of the present invention. The amount of the pyridine N-oxide compound contained in the ectoparasite control agent of the present invention is not particularly limited as long as its ectoparasite control effect is exhibited.

As the host animal to be treated with the ectoparasite control agent of the present invention, a warm-blooded animal such as a pet animal such as a dog and a cat; a pet bird; livestock such as a cow, a horse, a pig, and a sheep; and a fowl may be exemplified. In addition, a bee, a stag beetle and a beetle may be exemplified.

The ectoparasite control agent of the present invention may be applied by a known veterinary approach (local, oral, parenteral or subcutaneous administration).

As the method therefor, a method of orally administering tablets, capsules, feed or the like containing the ectoparasite control agent to animals; a method of administering the ectoparasite control agent through dipping liquids, suppositories, injection (intramuscular, subcutaneous, intravenous, or intraperitoneal injection, etc.) or the like to animals; a method of locally administering oily or aqueous liquid formulations by spraying, pour-on, spot-on or the like; and a method of kneading the ectoparasite control agent into a resin, shaping the kneaded product into a suitable shape such as a collar or an ear tag, and attaching it to animals for local administration; or the like may be exemplified.

Ectoparasites parasitize the inside or the body surface of host animals, particularly, warm-blooded animals. Specifically, the ectoparasites parasitize the backs, armpits, lower abdomens, inner thighs, or the like of host animals and live by obtaining nutrients such as blood or dandruff from the animals. As the ectoparasite, acari, lice, fleas, a mosquito, a stable fly, a flesh fly or the like may be exemplified. Specific examples of the ectoparasite controllable with the ectoparasite control agent of the present invention will be shown below.

(1) Acari

mites of the family Dermanyssidae, mites of the family Macronyssidae, mites of the family Laelapidae, mites of the family Varroidae, mites of the family Argasidae, mites of the family Ixodidae, mites of the family Psoroptidae, mites of the family Sarcoptidae, mites of the family Knemidokoptidae, mites of the family Demodixidae, mites of the family Trombiculidae, and insect parasitic mites such as mites of the family Canestriniidae. (2) The order Phthiraptera lice of the family Haematopinidae, lice of the family Linognathidae, bird lice of the family Menoponidae, bird lice of the family Philopteridae, and bird lice of the family Trichodectidae. (3) The order Siphonaptera fleas of the family Pulicidae, for example, Ctenocephalides canis and Ctenocephalides felis of Ctenocephalides spp.; fleas of the family Tungidae, fleas of the family Ceratophyllidae, and fleas of the family Leptopsyllidae. (4) The order Hemiptera (5) Insect pests of the order Diptera mosquitos of the family Culicidae, black flies of the family Simuliidae, biting midges of the family Ceratopogonidae, horseflies of the family Tabanidae, flies of the family Muscidae, tsetse flies of the family Glossinidae, flesh flies of the family Sarcophagidae, flies of the family Hippoboscidae, flies of the family Calliphoridae, and flies of the family Oestridae.

[Endoparasite Control Agent or Expellant]

The endoparasite control agent or expellant of the present invention contains at least one active ingredient selected from the pyridine N-oxide compounds of the present invention. The amount of the pyridine N-oxide compound contained in the endoparasite control agent or expellant of the present invention is not particularly limited as long as its endoparasite control effect is exhibited.

The parasite targeted by the endoparasite control agent or expellant of the present invention parasitizes the inside of host animals, particularly, warm-blooded animals or fishes (endoparasite). As the host animal for which the endoparasite control agent or expellant of the present invention is effective, a warm-blooded animal such as a human and a livestock mammal (e.g., a cow, a horse, a pig, a sheep, and a goat), a laboratory animal (e.g., a mouse, a rat, and a sand rat), a pet animal (e.g., a hamster, a guinea pig, a dog, a cat, a horse, a squirrel, a rabbit, and a ferret), wild and zoo mammals (e.g., a monkey, a fox, a deer, and a buffalo), a fowl (e.g., a turkey, a duck, a chicken, a quail, and a goose), and a pet bird (e.g., a pigeon, a parrot, a myna bird, a Java sparrow, a parakeet, a Bengalese finch, and a canary bird); and fishes such as a salmon, a trout, and a koi (carp) may be exemplified. Parasitic diseases mediated by parasites may be prevented or treated by controlling and expelling the parasites.

As the parasite to be controlled or expelled, the following may be exemplified.

(1) Nematodes of the order Dioctophymatida (a) kidney worms of the family Dioctophymatidae, for example, Dioctophyma renale of Dioctophyma spp.; (b) kidney worms of the family Soboliphymatidae, for example, Soboliphyme abei and Soboliphyme baturini of Soboliphyme spp. (2) Nematodes of the order Trichocephalida (a) trichinae of the family Trichinellidae, for example, Trichinella spiralis of Trichinella spp.; (b) whipworms of the family Trichuridae, for example, Capillaria annulata, Capillaria contorta, Capillaria hepatica, Capillaria perforans, Capillaria plica, and Capillaria suis of Capillaria spp.; and Trichuris vulpis, Trichuris discolor, Trichuris ovis, Trichuris skrjabini, and Trichuris suis of Trichuris spp. (3) Nematodes of the order Rhabditida threadworms of the family Strongyloididae, for example, Strongyloides papillosus, Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, and Strongyloides ratti of Strongyloides spp. (4) Nematodes of the order Strongylida hookworms of the family Ancylostomatidae, for example, Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma duodenale, and Ancylostoma tubaeforme of Ancylostoma spp.; Uncinaria stenocephala of Uncinaria spp.; and Bunostomum phlebotomum and Bunostomum trigonocephalum of Bunostomum spp. (5) Nematodes of the order Strongylida (a) nematodes of the family Angiostrongylidae, for example, Aelurostrongylus abstrusus of Aelurostrongylus spp.; and Angiostrongylus vasorum and Angiostrongylus cantonesis of Angiostrongylus spp.; (b) nematodes of the family Crenosomatidae, for example, Crenosoma aerophila and Crenosoma vulpis of Crenosoma spp.; (c) nematodes of the family Filaroididae, for example, Filaroides hirthi and Filaroides osleri of Filaroides spp.; (d) lungworms of the family Metastrongylidae, for example, Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus pudendotectus, and Metastrongylus salmi of Metastrongylus spp.; (e) gapeworms of the family Syngamidae, for example, Cyathostoma bronchialis of Cyathostoma spp.; and Syngamus skrjabinomorpha and Syngamus trachea of Syngamus spp. (6) Nematodes of the order Strongylida (a) nematodes of the family Molineidae, for example, Nematodirus filicollis and Nematodirus spathiger of Nematodirus spp.; (b) nematodes of the family Dictyocaulidae, for example, Dictyocaulus filaria and Dictyocaulus viviparus of Dictyocaulus spp.; (c) nematodes of the family Haemonchidae, for example, Haemonchus contortus of Haemonchus spp.; and Mecistocirrus digitatus of Mecistocirrus spp.; (d) nematodes of the family Haemonchidae, for example, Ostertagia ostertagi of Ostertagia spp.; (e) nematodes of the family Heligmonellidae, for example, Nippostrongylus braziliensis of Nippostrongylus spp.; (f) nematodes of the family Trichostrongylidae, for example, Trichostrongylus axei, Trichostrongylus colubriformis, and Trichostrongylus tenuis of Trichostrongylus spp.; Hyostrongylus rubidus of Hyostrongylus spp.; and Obeliscoides cuniculi of Obeliscoides spp. (7) Nematodes of the order Strongylida (a) nematodes of the family Chabertiidae, for example, Chabertia ovina of Chabertia spp.; and Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum venulosum, and Oesophagostomum watanabei of Oesophagostomum spp.; (b) nematodes of the family Stephanuridae, for example, Stephanurus dentatus of Stephanurus spp.; (c) nematodes of the family Strongylidae, for example, Strongylus asini, Strongylus edentatus, Strongylus equinus, and Strongylus vulgaris of Strongylus spp. (8) Nematodes of the order Oxyurida nematodes of the family Oxyuridae, for example, Enterobius anthropopitheci and Enterobius vermicularis of Enterobius spp.; Oxyuris equi of Oxyuris spp.; and Passalurus ambiguus of Passalurus spp. (9) Nematodes of the order Ascaridida (a) nematodes of the family Ascaridiidae, for example, Ascaridia galli of Ascaridia spp.; (b) nematodes of the family Heterakidae, for example, Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum, Heterakis pusilla, and Heterakis putaustralis of Heterakis spp.; (c) nematodes of the family Anisakidae, for example, Anisakis simplex of Anisakis spp.; (d) nematodes of the family Ascarididae, for example, Ascaris lumbricoides and Ascaris suum of Ascaris spp.; and Parascaris equorum of Parascaris spp.; (e) nematodes of the family Toxocaridae, for example, Toxocara canis, Toxocara leonina, Toxocara suum, Toxocara vitulorum, and Toxocara cati of Toxocara spp. (10) Nematodes of the order Spirurida (a) nematodes of the family Onchocercidae, for example, Brugia malayi, Brugia pahangi, and Brugia patei of Brugia spp.; Dipetalonema reconditum of Dipetalonema spp.; Dirofilaria immitis of Dirofilaria spp.; Filaria oculi of Filaria spp.; and Onchocerca cervicalis, Onchocerca gibsoni, and Onchocerca gutturosa of Onchocerca spp.; (b) nematodes of the family Setariidae, for example, Setaria digitata, Setaria equina, Setaria labiatopapillosa, and Setaria marshalli of Setaria spp.; and Wuchereria bancrofti of Wuchereria spp.; (c) nematodes of the family Filariidae, for example, Parafilaria multipapillosa of Parafilaria spp.; and Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, and Stephanofilaria stilesi of Stephanofilaria spp. (11) Nematodes of the order Spirurida (a) nematodes of the family Gnathostomatidae, for example, Gnathostoma doloresi and Gnathostoma spinigerum of Gnathostoma spp.; (b) nematodes of the family Habronematidae, for example, Habronema majus, Habronema microstoma, and Habronema muscae of Habronema spp.; and Draschia megastoma of Draschia spp.; (c) nematodes of the family Physalopteridae, for example, Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaloptera rara, Physaloptera sibirica, and Physaloptera vulpineus of Physaloptera spp.; (d) nematodes of the family Gongylonematidae, for example, Gongylonema pulchrum of Gongylonema spp.; (e) nematodes of the family Spirocercidae, for example, Ascarops strongylina of Ascarops spp.; (f) nematodes of the family Thelaziidae, for example, Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Thelazia rhodesi, and Thelazia skrjabini of Thelazia spp.

[Control Agent for Other Pests]

The pyridine N-oxide compound of the present invention is additionally excellent in control effect on insect pests that have a stinger or a venom and harm humans and animals, insect pests that mediate various pathogens or disease-causing microbes, or insect pests that cause discomfort to humans (toxic pests, unhygienic pests, and obnoxious pests, etc.).

Specific examples thereof will be shown below.

(1) Insect pests of the order Hymenoptera bees of the family Argidae, bees of the family Cynipidae, bees of the family Diprionidae, ants of the family Formicidae, bees of the family Mutillidae, and bees of the family Vespidae. (2) Other insect pests Blattodea, termites, Araneae, centipedes, millipedes, crustacea, and Cimex lectularius.

[Soil Treatment Agent]

Soil treatment in the present invention is, for example, a method for controlling pests directly or controlling pests with the active ingredient allowed to penetrate and migrate from a root, etc. in a plant body by applying an active ingredient to the rhizosphere of the plant to be protected from harm such as eating by pests. For example, planting hole treatment (planting hole spraying, and planting hole treatment and soil mixture), plant foot treatment (plant foot spraying, plant foot soil mixture, plant foot irrigation, and plant foot treatment in the latter half of a seedling raising period), planting groove treatment (planting groove spraying and planting groove soil mixture), furrow treatment (furrow spraying, furrow soil mixture, and furrow spraying in a growing period), furrow treatment at the time of sowing (furrow spraying at the time of sowing and furrow soil mixture at the time of sowing), whole surface treatment (whole surface soil spraying and whole surface soil mixture), side row treatment, water surface treatment (whole water surface application and frame water surface application), other soil spraying treatment (spraying a granular agent on the surfaces of leaves in a growing period, spraying under a tree crown or on the periphery of a trunk, soil surface spraying, soil surface mixture, sowing hole spraying, spraying on the surface of the earth in ridges, and spraying between roots), other irrigation treatment (soil irrigation, irrigation in a seedling raising period, chemical feeding treatment, irrigation at a portion near the surface of the ground, chemical drip irrigation, and chemigation), seedling box treatment (seedling box spraying, seedling box irrigation, and filling a seedling box with a chemical), seedbed treatment (seedbed spraying, seedbed irrigation, and flooded nursery seedbed spraying), seedling immersion, seedling-raising, ridging and mixture treatment (bed soil mixture and soil covering and mixture), spraying at the time of sowing before soil covering, spraying at the time of sowing after soil covering, stem injection treatment, trunk injection treatment, trunk spraying treatment, and other treatment (plowing, surface soil mixture, mixture at a portion that rain strikes, planting location treatment, spraying a granular agent on flower clusters, and paste fertilizer mixture) are specifically exemplified. The soil treatment agent of the present invention is preferably a soil irrigation treatment agent.

[Pharmaceutical Formulation]

Some pharmaceutical formulations of the pest control agent, the insecticide or acaricide, the ectoparasite control agent or the endoparasite control agent or expellant of the present invention will be shown. However, additives and addition ratios should not be limited by these examples and may be changed in wide ranges. The term “part” in the pharmaceutical formulations represents part by weight.

Hereinafter, the pharmaceutical formulations for agriculture or horticulture and for paddy rice will be shown.

(Preparation 1: Wettable Powder:Hydrate)

40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfuric acid ester, and 3 parts of alkyl naphthalenesulfonate are uniformly mixed and finely milled to obtain a wettable powder containing 40% of the active ingredient.

(Preparation 2: Emulsion)

30 parts of the compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl aryl ether are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.

(Preparation 3: Granular Formulation)

5 parts of the compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed, finely milled, and then granulated into a granular shape of 0.5 to 1.0 mm in diameter to obtain a granular formulation containing 5% of the active ingredient.

(Preparation 4: Granular Formulation)

5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate are well milled and mixed, and after addition of water, the mixture is well kneaded, then granulated, and dried to obtain a granular formulation containing 5% of the active ingredient.

(Preparation 5: Suspension)

10 parts of the compound of the present invention, 4 parts of polyoxyethylene alkyl aryl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-milled until the particle size becomes 3 microns or smaller to obtain a suspension containing 10% of the active ingredient.

Hereinafter, the pharmaceutical formulations of the ectoparasite control agent or the endoparasite control agent or expellant will be shown.

(Preparation 6: Granules)

5 parts of the compound of the present invention are dissolved in an organic solvent to obtain a solution. The solution is sprayed onto 94 parts of kaolin and 1 part of white carbon. Then, the solvent is evaporated under reduced pressure. This type of granules may be mixed with animal feed.

(Preparation 7: Injectable Filler)

0.1 to 1 parts of the compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed and then sterilized by filtration through a sterilizing filter.

(Preparation 8: Pore-On Formulation)

5 parts of the compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol are uniformly mixed to obtain a pore-on formulation.

(Preparation 9: Spot-On Formulation)

10 to 15 parts of the compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol are uniformly mixed to obtain a spot-on formulation.

(Preparation 10: Spray Formulation)

1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol are uniformly mixed to obtain a spray formulation.

Next, the present invention will be more specifically described with reference to Examples of compounds. However, the present invention is not limited by the following Examples of compounds by any means.

EXAMPLE 1 Synthesis of 5-cyclopropyl-3-(ethylsulfonyl)-2-(5-((trifluoromethyl)sulfonyl)benzo[d]oxazol-2-yl)pyridine 1-oxide (Compound No. A-1)

First, 2-(5-cyclopropyl-3-(ethylsulfonyl)pyridine-2-yl)-5-(trifluoromethyl)sulfinyl)benzo[d]oxazol (0.16 g) synthesized by a method described in International Publication No. WO 2017/146226A was dissolved in chloroform (2.5 ml), and the mixture was stirred at room temperature. Meta-chloroperoxybenzoic acid (65%, 0.26 g) was added to this, and the mixture was stirred at room temperature overnight and then stirred at 50° C. for 5 hours. The obtained solution was poured to a mixed solution of a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate, followed by extraction with dichloromethane. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.08 g (yield: 48%) of the title compound.

¹H-NMR and the melting point of the obtained title compound will be shown below.

¹H-NMR (400 MHz, CDCl₃): δ 8.55 (s, 1H), 8.27 (d, 1H), 8.17 (d, 1H), 7.94 (d, 1H), 7.57 (d, 1H), 3.54 (q, 2H), 2.06-1.99 (m, 1H), 1.39-1.33 (m, 5H), 0.97-0.95 (m, 2H).

Melting point: 210 to 212° C.

[Biological Test]

Test Examples given below show that the compound of the present invention is useful as an active ingredient for pest control agents and ectoparasite control agents. The term “part” is based on weight.

(Preparation of Test Emulsion)

5 parts of the compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to prepare emulsion (I) containing 5% of the active ingredient.

For a control, 93.6 parts of dimethylformamide and 1.4 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to prepare emulsion (II).

An insecticidal rate was calculated according to the following expression:

Insecticidal rate (%)=(The number of dead insects/The number of tested insects)×100

A control rate was calculated according to the following expression:

Control rate (%)={1−(Nt)/(Nc)}×100

Nc: The number of parasites in an untreated plot

Nt: The number of parasites in a spray treated plot

(Test Example 1) Test of Efficacy on Mythimna separata

0.8 g of commercially available artificial feed (Insecta LFS, manufactured by Nosan Corp.) and 1 μl of the emulsion (I) were well mixed to obtain test feed.

A plastic test container (capacity: 1.4 ml) was packed with 0.2 g of the test feed per treatment plot. Then, two second instar larvae of Mythimna separata were inoculated to each treatment plot. A plastic lid was put on the test container so as to prevent escape of the second instar larvae of Mythimna separata. The container was placed in a thermostat chamber of 25° C. On the fifth day, the insecticidal rate and the food intake were examined. The test was conducted in duplicate.

The insecticidal rate and the food intake of a control plot were examined in the same way as in Test Example 1 except that the emulsion (I) was changed to the emulsion (II).

A compound of compound No. A-1 was tested for its efficacy on Mythimna separata. The compound had an insecticidal rate of 100% for Mythimna separata or a food intake of 10% or less as compared with the control plot.

(Test Example 2) Test of Efficacy on Plutella xylostella

The emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were dipped in the dilution for 30 seconds. The resulting cabbage leaves were placed in a petri dish. Five second instar larvae of Plutella xylostella were released thereto. The petri dish was placed in a thermostat chamber having a temperature of 25° C. and a humidity of 60%. Life and death were determined after 3 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

The compound of compound No. A-1 was tested for its efficacy on Plutella xylostella. The compound exhibited an insecticidal rate of 80% or more for Plutella xylostella.

(Test Example 3) Test of Efficacy on Aphis craccivora

Seedlings of black-eyed peas were raised in 10-cm pots. Aphis craccivora nymphs were inoculated onto primary leaves. The emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 125 ppm. The dilution was sprayed to the black-eyed peas parasitized by the Aphis craccivora nymphs. The black-eyed peas were placed in a thermostat chamber having a temperature of 25° C. and a humidity of 60%. Life and death of Aphis craccivora were determined after 4 days from the spraying, and the insecticidal rate was calculated. The test was conducted in duplicate.

The compound of compound No. A-1 was tested for its efficacy on Aphis craccivora. The compound exhibited an insecticidal rate of 80% or more for Aphis craccivora.

(Test Example 4) Test of Efficacy on Aphis gossypii

Cucumbers were sown in a 10-cm pot. An Aphis gossypii female adult was released to the cucumbers after 10 days from sprouting. On the next day, born first instar larvae were left, and the female adult was removed. Emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 125 ppm. The dilution was sprayed to the cucumbers. The cucumbers were placed in a thermostat chamber having a temperature of 25° C. and a humidity of 60%. Life and death of Aphis gossypii were determined after 5 days, and the insecticidal rate was calculated.

The compound of compound No. A-1 was tested for its efficacy on Aphis gossypii. The compound exhibited an insecticidal rate of 80% or more for Aphis gossypii.

(Test Example 5) Test of Efficacy on Phyllotreta striolata

The emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 125 ppm to prepare a test chemical. The dilution was sprayed to Qing geng cai seedlings (at the seventh true leaf stage) planted in 10-cm pots. The Qing geng cai seedlings were dried in air and then placed in a plastic cup. Ten Phyllotreta striolata adults were released thereto. The plastic cup was stored in a thermostat chamber having a temperature of 25° C. and a humidity of 65%. Life and death were determined after 7 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

The compound of compound No. A-1 was tested for its efficacy on Phyllotreta striolata adults. The compound exhibited an insecticidal rate of 80% or more for Phyllotreta striolata adults.

(Test Example 6) Test of Efficacy on Musca domestica

The compound of the present invention was diluted with acetone, and the dilution was added dropwise to 1 g of lump sugar such that the concentration was 100 ppm. The lump sugar was placed in a plastic cup, ten Musca domestica female adults were released, and a lid was put on the cup. The plastic cup was stored at 25° C. Life and death were determined after 24 hours from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

The compound of compound No. A-1 was tested for its efficacy on Musca domestica. The compound exhibited an insecticidal rate of 80% or more for Musca domestica.

(Test Example 7) Test of Soil Irrigation Treatment Against Plutella xylostella

The emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 500 ppm or 250 ppm. Then, 500 mL of the dilution was subjected to irrigation treatment per 128-hole cell tray in which cabbage seedlings were planted. The cell seedlings were transplanted to No. 4 pots and maintained in a thermostat chamber having a temperature of 25° C. and a humidity of 65%. Then, 50 first instar larvae of Plutella xylostella were inoculated on the whole of a cabbage after 21 days and 28 days from the transplant, respectively.

The life and the death of Plutella xylostella were investigated after 3 days, and a control rate was calculated according to the following expression. The test was conducted in quadruplicate.

Control rate (%)={1−(Nt)/(Nc)}×100

Nc: The number of parasites in an untreated plot

Nt: The number of parasites in a spray treated plot

The compound of compound No. A-1 was subjected to the test of soil irrigation treatment against Plutella xylostella. The results were shown in Table 5.

TABLE 5 Control rate % Compound 21 days 28 days No. Concentration after after A-1 500 ppm 100 100 250 ppm 98 99

All the compounds selected at random from among the pyridine N-oxide compounds of the present invention exerted the effect as described above. It may therefore be understood that the pyridine N-oxide compound of the present invention, including unillustrated compounds, is a compound having an effect such as a pest control effect, particularly, an acaricidal or insecticidal effect. It may also be understood that the pyridine N-oxide compound of the present invention is a compound also having an effect on parasites harmful to humans and animals, such as ectoparasites. 

1. A compound of formula (II), a stereoisomer, tautomer or hydrate thereof or a salt of any of these compounds:

wherein R¹ represents a substituted or unsubstituted C1-6 alkylsulfonyl group; R² represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, or a halogeno group; A¹ represents an oxygen atom, a sulfur atom, or NR³; R³ represents a hydrogen atom or a C1-6 alkyl group; A² and A³ each independently represent a carbon atom or a nitrogen atom; X represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, or a substituted or unsubstituted C1-6 alkylsulfonyl group; n represents a number of chemically acceptable Xs, and is an integer of 0 to 2; and Xs are the same or different when n is
 2. 2. The compound according to claim 1, a stereoisomer, tautomer or hydrate thereof or a salt of any of these compounds, wherein the formula (II) is formula (I):

wherein R¹, R², X, and n represent the same meanings as described in the formula (II).
 3. A pest control agent comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, a stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 4. An insecticide or acaricide comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, a stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 5. An ectoparasite control agent comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, a stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 6. An endoparasite control agent or expellant comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, a stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.
 7. A soil treatment agent comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, a stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds. 